As a young girl, Sally Singer was “obsessed” with fashion. She crafted unique looks from vintage items and even sewed her own clothing using Vogue as her trusty guide. Little did she know she would not only work for the magazine one day, she would also build a storied career centered on her exceptional taste in clothing.

“You have to be someone who obsesses over the statement, scale, and purpose of fashion to work in it for this long,” said Singer, who joined Amazon in 2019 after two decades leading editorial and digital teams at Vogue. “The privilege of working in this industry is having real relationships with people who are the best in the world at what they do. I've been lucky to attend exciting events and fashion shows, but I feel most fortunate to have spent real time with the most fascinating, creative people in the industry.”

An image of Sally Singer smiling for a photo at a black tie event. There are two men smiling for the photo alongside her.
Singer with designers Chris Kane and Erdem Moralıoğlu

In her role as head of Amazon Fashion Direction, Singer advises across teams that are innovating for fashion at the company. No two days look the same, as she applies her fine-tuned sense of style and editorial instinct to help provide more engaging, exciting, and inclusive experiences for customers around the world. We met with Singer to learn more about her career and her vision for Amazon Fashion. Keep reading to find out how she has helped shape the Amazon Fashion shopping experience.

What has it been like shifting your mindset from the 'Vogue' customer to the Amazon customer?

Shifting focus from the Vogue customer to the Amazon customer isn't as difficult as people would think. I’ve spent many years talking to retailers about what sells and what doesn't, and the pain points are nearly always the same for customers. They want to know why something has value and why they should invest in it. This applies to someone who's spending $49 on a jacket just as much as it does to someone who's spending $4,000. I think the real challenge at Amazon is to add storytelling and humanity to the storefront that most people think of as strictly utilitarian. Shopping on Amazon can become a habit, and it’s meant to be efficient, but we also want to make Amazon Fashion a place of discovery, where customers can experience a sense of pleasure, security, and all of the other feelings fashion can bring about.

What kind of storytelling has gone into Amazon Fashion’s efforts to earn trust with customers?

We’ve implemented people-first storytelling and embrace the idea that Amazon Fashion is for everyone. Whatever you want fashion to do for you—whether the goal is to blend in or stand out—we have something for you somewhere on this site, and we can get it to you quickly. Our creative teams focus on telling stories of how customers wear clothes their way. Instead defaulting to models, we're now showing really interesting people looking fabulous in clothing they bought on Amazon.

Welcome to our series "Real (cool) jobs at Amazon," where we highlight talented people with exciting jobs at Amazon.

What is your favorite project you’ve worked on at Amazon so far?

We released an Amazon Fashion gift guide for the 2021 holiday season with the goal of featuring different types of people from around the country. We styled the people in the catalog to look like themselves. So, for example, you meet these amazing sisters who are hip-hop performers from Michigan, wearing metallic puffers covered with sparkly broaches, metallic knife-pleated skirts, and floral Doc Martens—a fabulous look. It was runway-worthy and all of the products were from Amazon; i.e., inexpensive products, but worn the way these women actually wear clothes.

A catalog image showing the two women Sally mentions above. Next to the page with their image is another page with outfit options.
An image of women smiling while holding their hands in the air. They are wearing coordinated holiday sweaters. Text on the page reads "Close knits."
An image of two pages of a catalog. One page shows a selection of flannel shirts with text that reads "Holiday Check List" and the other is a man who is in a wheelchair wearing a flannel shirt petting his dog.
An image of people in a drumline wearing matching red track suits. On the other side of the catalog you see text that reads "Dress to your own beat; relax into your own rhythm.
A catalog image of a woman skateboarding. Next to her image is text that reads "When I skate, I get to breathe, relax, recharge. It's so freeing to me."

Have you seen any promising feedback from customers about that gift guide?

We’ve seen some exciting responses. The gift guide featured a fellow who is in a wheelchair modeling a selection of flannel shirts alongside his dog. We received so many comments on Instagram from people saying “Thank you for showing this picture,” because it meant a lot to them to see people with various abilities represented in an authentic way. We also featured an Indigenous woman who's a skateboarder in this holiday gift guide, and we had so much joy in the comments on Instagram from people who were excited because we had recognized her very special style. Amazon’s strength is in its universality, and that means we’ll continue finding ways to show a universal view of the world.

What advice do you have for developing an authentic sense of style?

I've always thought style is a person’s sense of who they are, or at least the outward expression of it. Often, this comes from an image of grown-ups they had when they were much younger, from when they were 13 and looked up and said, “I want to look like that person. That's a cool grown-up.” And so, their aspiration always leans that way. When you can figure out what your aspiration is, you can begin to touch some of that magic. I always try to get people to understand the root of the dream for them—not literally looking at a picture and saying, “I want to wear that, but I can't because I'm not that size, or I'm not that age, or I'm not that rich.” I just want them to figure out what the essence of it is. I'm interested in a world where you imagine what you're going to be and find a way to get a bit of that, regardless of the rest. Having that bit of magic in your clothes means you can wear the same thing every day with slight tweaks and still feel great.

An image of Sally Singer standing in a room with blue wallpaper and interesting art on the walls. She is sipping a cold drink from a Starbucks cup and looking out the window.

What is your best piece of advice for dressing up, as many of us are returning to events and outings for the first time in two years?

I always say this for people around eveningwear: it should come from a place of comfort. We all have clothing that really makes us feel like ourselves—whether it’s pajamas, a nightgown, a muumuu, or a minidress. When people go to evening or other formal wear, they often forget that thing, and they go to some idea of fancy that has nothing to do with their comfort zone. Appreciate your comfort zone, it has a place in your life. A great example of this is Kristen Stewart at the Oscars in those Chanel hot pants. She likes her legs and she doesn't need to wear a ball gown. That's why she wore shorts to the Oscars. Find the thing that you actually like and just “up it” for the event—don’t try to reinvent yourself on a big night.

What are your favorite finds on Amazon Fashion?

I buy a lot of retro-inspired sneakers for myself and for my sons—specifically Adidas—from Amazon. I also wear a lot of Levi's from Amazon (I really like a pair of white Levi’s). While I buy a lot of essentials, which Amazon does very well, I’m also excited about what we've done in the Luxury Stores program with exclusives. I bought sporty men's shirts from Perfect Moment, and I also have a bunch of Rodarte from Amazon—beautiful blouses and floral dresses, and I also love their sweats. I have a lot of fun summer frocks and sparkly shoes from Amazon sellers as well. I look at the customer reviews for every purchase. As a customer, I listen and learn from other customers!

What advice do you have for others who aspire to a career like yours?

Don’t prioritize ambition for ambition’s sake. Doing what everyone else is doing won’t get you anywhere anyway. Enjoy the experience of living. Don't spend a whole lot of time chasing a title and money. That will come if you find what you love and enjoy the process. I know so many people who have probably had more celebrated careers than me … but they haven't had as much fun.

If you enjoyed learning about Sally Singer's work at Amazon, read more articles from this series. For more information about opportunities at the company, visit